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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-18 08:36:36 UTC
Update Date2021-10-13 04:36:26 UTC
HMDB IDHMDB0001925
Secondary Accession Numbers
  • HMDB0001872
  • HMDB01872
  • HMDB01925
Metabolite Identification
Common NameIbuprofen
DescriptionIbuprofen is a nonsteroidal anti-inflammatory drug (NSAID) widely marketed under various trademarks including Act-3, Advil, Brufen, Motrin, Nuprin, and Nurofen. It is used for relief of symptoms of arthritis, primary dysmenorrhoea, and fever; Ibuprofen is an NSAID which is believed to work through inhibition of cyclooxygenase (COX), thus inhibiting prostaglandin synthesis. There are at least 2 variations of cyclooxygenase (COX-1 and COX-2), ibuprofen inhibits both COX-1 and COX-2. It appears that its analgesic, antipyretic, and anti-inflammatory activity are achieved principally through COX-2 inhibition; whereas COX-1 inhibition is responsible for its unwanted effects on platelet aggregation and the GI mucosa. As with other NSAIDs, ibuprofen inhibits platelet aggregation, but is not used therapeutically for this action since it is a minor and reversible effect. -- Wikipedia .
Structure
Data?1582752217
Synonyms
ValueSource
(+-)-2-(p-Isobutylphenyl)propionic acidChEBI
(+-)-alpha-Methyl-4-(2-methylpropyl)benzeneacetic acidChEBI
(+-)-IbuprofenChEBI
(+-)-p-Isobutylhydratropic acidChEBI
(4-Isobutylphenyl)-alpha-methylacetic acidChEBI
(RS)-IbuprofenChEBI
2-(4-Isobutylphenyl)propanoic acidChEBI
4-Isobutylhydratropic acidChEBI
AdranChEBI
AdvilChEBI
alpha-(4-Isobutylphenyl)propionic acidChEBI
alpha-(p-Isobutylphenyl)propionic acidChEBI
AmibufenChEBI
AncoChEBI
AnflagenChEBI
ApsifenChEBI
BlutonChEBI
BrufenChEBI
BrufortChEBI
BuburoneChEBI
ButyleninChEBI
DolginChEBI
DolgiridChEBI
DolgitChEBI
Dolo-dolgitChEBI
EbufacChEBI
EpobronChEBI
FemadonChEBI
HaltranChEBI
Ibu-attritinChEBI
IbumetinChEBI
IbuprocinChEBI
IbutidChEBI
InabrinChEBI
InovenChEBI
LamidonChEBI
LebrufenChEBI
LiptanChEBI
MediprenChEBI
MotrinChEBI
MynosedinChEBI
NobfenChEBI
NobgenChEBI
NuprinChEBI
NurofenChEBI
PediaprofenChEBI
RoideninChEBI
RufenChEBI
SeclodinChEBI
SusprenChEBI
TabalonChEBI
TrendarChEBI
UremChEBI
(+-)-2-(p-Isobutylphenyl)propionateGenerator
(+-)-a-Methyl-4-(2-methylpropyl)benzeneacetateGenerator
(+-)-a-Methyl-4-(2-methylpropyl)benzeneacetic acidGenerator
(+-)-alpha-Methyl-4-(2-methylpropyl)benzeneacetateGenerator
(+-)-Α-methyl-4-(2-methylpropyl)benzeneacetateGenerator
(+-)-Α-methyl-4-(2-methylpropyl)benzeneacetic acidGenerator
(+-)-p-IsobutylhydratropateGenerator
(4-Isobutylphenyl)-a-methylacetateGenerator
(4-Isobutylphenyl)-a-methylacetic acidGenerator
(4-Isobutylphenyl)-alpha-methylacetateGenerator
(4-Isobutylphenyl)-α-methylacetateGenerator
(4-Isobutylphenyl)-α-methylacetic acidGenerator
2-(4-Isobutylphenyl)propanoateGenerator
4-IsobutylhydratropateGenerator
a-(4-Isobutylphenyl)propionateGenerator
a-(4-Isobutylphenyl)propionic acidGenerator
alpha-(4-Isobutylphenyl)propionateGenerator
Α-(4-isobutylphenyl)propionateGenerator
Α-(4-isobutylphenyl)propionic acidGenerator
a-(p-Isobutylphenyl)propionateGenerator
a-(p-Isobutylphenyl)propionic acidGenerator
alpha-(p-Isobutylphenyl)propionateGenerator
Α-(p-isobutylphenyl)propionateGenerator
Α-(p-isobutylphenyl)propionic acidGenerator
alpha-p-IsobutylphenylpropionateHMDB
alpha-p-Isobutylphenylpropionic acidHMDB
DuralbuprofenHMDB
p-Isobutyl-2-phenylpropionateHMDB
p-Isobutyl-2-phenylpropionic acidHMDB
p-IsobutylhydratropateHMDB
p-Isobutylhydratropic acidHMDB
Calcium salt ibuprofenHMDB
Ibuprofen, copper (2+) saltHMDB
Ibuprofen, magnesium saltHMDB
Ibuprofen, zinc saltHMDB
Trauma dolgit gelHMDB
Aluminum salt ibuprofenHMDB
IP 82HMDB
Ibuprofen, aluminum saltHMDB
Ibuprofen-zincHMDB
Magnesium salt ibuprofenHMDB
Salt ibuprofen, magnesiumHMDB
Sodium salt ibuprofenHMDB
Zinc salt ibuprofenHMDB
I.V. solution, ibuprofenHMDB
IP-82HMDB
Ibuprofen i.v. solutionHMDB
Ibuprofen, (+-)-isomerHMDB
Ibuprofen, (R)-isomerHMDB
Ibuprofen, (S)-isomerHMDB
Ibuprofen, calcium saltHMDB
Potassium salt ibuprofenHMDB
SalprofenHMDB
Salt ibuprofen, sodiumHMDB
Salt ibuprofen, zincHMDB
alpha-Methyl-4-(2-methylpropyl)benzeneacetic acidHMDB
Ibuprofen zincHMDB
Ibuprofen, potassium saltHMDB
Ibuprofen, sodium saltHMDB
Trauma-dolgit gelHMDB
TraumaDolgit gelHMDB
Chemical FormulaC13H18O2
Average Molecular Weight206.2808
Monoisotopic Molecular Weight206.13067982
IUPAC Name2-[4-(2-methylpropyl)phenyl]propanoic acid
Traditional Nameibuprofen, (+-)-
CAS Registry Number15687-27-1
SMILES
CC(C)CC1=CC=C(C=C1)C(C)C(O)=O
InChI Identifier
InChI=1S/C13H18O2/c1-9(2)8-11-4-6-12(7-5-11)10(3)13(14)15/h4-7,9-10H,8H2,1-3H3,(H,14,15)
InChI KeyHEFNNWSXXWATRW-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassPhenylpropanoic acids
Sub ClassNot Available
Direct ParentPhenylpropanoic acids
Alternative Parents
Substituents
  • 2-phenylpropanoic-acid
  • P-cymene
  • Aromatic monoterpenoid
  • Monocyclic monoterpenoid
  • Monoterpenoid
  • Phenylpropane
  • Monocyclic benzene moiety
  • Benzenoid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Carbonyl group
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Adverse health effect

Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point76 °CNot Available
Boiling Point319.60 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility0.021 mg/mL at 25 °CNot Available
LogP3.97AVDEEF,A (1997)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available143.984http://allccs.zhulab.cn/database/detail?ID=AllCCS00001393
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.068 g/LALOGPS
logP10(3.5) g/LALOGPS
logP10(3.84) g/LChemAxon
logS10(-3.5) g/LALOGPS
pKa (Strongest Acidic)4.85ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity60.73 m³·mol⁻¹ChemAxon
Polarizability23.76 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+150.26731661259
DarkChem[M-H]-148.48431661259
AllCCS[M+H]+146.58732859911
AllCCS[M-H]-151.55532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
IbuprofenCC(C)CC1=CC=C(C=C1)C(C)C(O)=O2622.1Standard polar33892256
IbuprofenCC(C)CC1=CC=C(C=C1)C(C)C(O)=O1591.8Standard non polar33892256
IbuprofenCC(C)CC1=CC=C(C=C1)C(C)C(O)=O1633.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Ibuprofen,1TMS,isomer #1CC(C)CC1=CC=C(C(C)C(=O)O[Si](C)(C)C)C=C11614.9Semi standard non polar33892256
Ibuprofen,1TBDMS,isomer #1CC(C)CC1=CC=C(C(C)C(=O)O[Si](C)(C)C(C)(C)C)C=C11858.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Ibuprofen GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-02t9-1910000000-23f448d7be7d5cc356822014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ibuprofen GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-02t9-1910000000-cbe52d63986b68a2cec02014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ibuprofen GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-00di-9300000000-cc259b7768023e4cdba82014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ibuprofen EI-B (Non-derivatized)splash10-03di-3910000000-618880f8fd7b8ec3d4732017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ibuprofen GC-EI-TOF (Non-derivatized)splash10-02t9-1910000000-23f448d7be7d5cc356822017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ibuprofen GC-EI-TOF (Non-derivatized)splash10-02t9-1910000000-cbe52d63986b68a2cec02017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ibuprofen GC-EI-TOF (Non-derivatized)splash10-00di-9300000000-cc259b7768023e4cdba82017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ibuprofen GC-MS (Non-derivatized) - 70eV, Positivesplash10-0296-3900000000-497aad6d6a3e7af1ac0a2017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ibuprofen GC-MS (1 TMS) - 70eV, Positivesplash10-0309-8940000000-13dc492b216fb21dde052017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ibuprofen GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ibuprofen GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ibuprofen GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-03xr-3900000000-e20ef3c30496e17720ba2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Ibuprofen Quattro_QQQ 10V, N/A-QTOF (Annotated)splash10-03di-0910000000-90bf6813134491c9fbfd2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ibuprofen Quattro_QQQ 25V, N/A-QTOF (Annotated)splash10-001i-9800000000-56f599abc462380b648c2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ibuprofen EI-B (HITACHI RMU-6E) , Positive-QTOFsplash10-03di-3910000000-618880f8fd7b8ec3d4732012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ibuprofen LC-ESI-qTof , Positive-QTOFsplash10-0006-0497000000-fa397d6ffd29da1169002017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ibuprofen LC-ESI-qTof , Positive-QTOFsplash10-0a4i-0690000000-f598b8bee69a6b62e8172017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ibuprofen , positive-QTOFsplash10-03di-1900000000-f1b7a986fee133d97eb12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ibuprofen , positive-QTOFsplash10-03di-0920000000-aa36b3244e32560bb9d52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ibuprofen 10V, Negative-QTOFsplash10-03di-0900000000-5542c131f02b637029d82021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ibuprofen 40V, Negative-QTOFsplash10-03di-9200000000-5de1fac09e33bce1cc342021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ibuprofen 30V, Negative-QTOFsplash10-0a4i-0900000000-c254195738a6348894be2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ibuprofen 10V, Negative-QTOFsplash10-0a4i-0900000000-d4b4b28d0bf1144854c32021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ibuprofen 15V, Negative-QTOFsplash10-0a4i-0900000000-5f5841ab0d19d92f329f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ibuprofen 20V, Negative-QTOFsplash10-03dl-7900000000-811cee3d7fc26d62724a2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ibuprofen 10V, Positive-QTOFsplash10-0a4i-1970000000-50ac0f9eaf22b22ff57f2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ibuprofen 20V, Positive-QTOFsplash10-0bti-2910000000-a5804838ebd627fea2052017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ibuprofen 40V, Positive-QTOFsplash10-0pb9-4900000000-a5b30d0a96d30db5ea4a2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ibuprofen 10V, Negative-QTOFsplash10-0a4i-0490000000-27a27175d7bf2807ff332017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ibuprofen 20V, Negative-QTOFsplash10-08fr-1940000000-f33172b037148de8a0912017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ibuprofen 40V, Negative-QTOFsplash10-02ha-5900000000-ebc408aaffe3ab58a6a32017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ibuprofen 10V, Positive-QTOFsplash10-0bti-0930000000-d13739453cc1a7af33072021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ibuprofen 20V, Positive-QTOFsplash10-0bud-2910000000-db9b1bc4f7d1e33abb3c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ibuprofen 40V, Positive-QTOFsplash10-0006-9510000000-6eaaec80d704e4b4603c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ibuprofen 10V, Negative-QTOFsplash10-0a4i-0090000000-5535f56d1e770e37902d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ibuprofen 20V, Negative-QTOFsplash10-08fr-0900000000-1aedbd14d6db0c13aa632021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ibuprofen 40V, Negative-QTOFsplash10-014i-0900000000-9537810cacf26548c24a2021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Locations
  • Adipose Tissue
  • Adrenal Cortex
  • Adrenal Gland
  • Bladder
  • Epidermis
  • Fibroblasts
  • Intestine
  • Kidney
  • Neuron
  • Pancreas
  • Placenta
  • Platelet
  • Prostate
  • Skeletal Muscle
  • Spleen
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified242.0 (2.42-485.0) uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified6.513 +/- 6.212 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified1.528 +/- 0.563 uMAdult (>18 years old)Bothnerve root compression pain details
Cerebrospinal Fluid (CSF)Detected and Quantified0.815 +/- 0.296 uMAdult (>18 years old)Bothnerve root compression pain details
Cerebrospinal Fluid (CSF)Detected and Quantified0.000592 +/- 0.000170 uMAdult (>18 years old)BothBronchial carcinoma details
UrineDetected and Quantified3.408 +/- 2.229 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
details
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease References
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Associated OMIM IDs
DrugBank IDDB01050
Phenol Explorer Compound IDNot Available
FooDB IDFDB022743
KNApSAcK IDNot Available
Chemspider ID3544
KEGG Compound IDC01588
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkIbuprofen
METLIN ID572
PubChem Compound3672
PDB IDNot Available
ChEBI ID5855
Food Biomarker OntologyNot Available
VMH IDIBUP_R
MarkerDB IDNot Available
Good Scents IDrw1204091
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Perioli L, Ambrogi V, Angelici F, Ricci M, Giovagnoli S, Capuccella M, Rossi C: Development of mucoadhesive patches for buccal administration of ibuprofen. J Control Release. 2004 Sep 14;99(1):73-82. [PubMed:15342182 ]
  2. Whitlam JB, Brown KF, Crooks MJ, Room GF: Transsynovial distribution of ibuprofen in arthritic patients. Clin Pharmacol Ther. 1981 Apr;29(4):487-92. [PubMed:7471614 ]
  3. Al-Saidan SM: Transdermal self-permeation enhancement of ibuprofen. J Control Release. 2004 Nov 24;100(2):199-209. [PubMed:15544868 ]
  4. Albert KS, Gernaat CM: Pharmacokinetics of ibuprofen. Am J Med. 1984 Jul 13;77(1A):40-6. [PubMed:6465162 ]
  5. Alam I, Ferrell LD, Bass NM: Vanishing bile duct syndrome temporally associated with ibuprofen use. Am J Gastroenterol. 1996 Aug;91(8):1626-30. [PubMed:8759674 ]
  6. Townsend RJ, Benedetti TJ, Erickson SH, Cengiz C, Gillespie WR, Gschwend J, Albert KS: Excretion of ibuprofen into breast milk. Am J Obstet Gynecol. 1984 May 15;149(2):184-6. [PubMed:6720796 ]
  7. Horn AC, Jarrett SW: Ibuprofen-induced aseptic meningitis in rheumatoid arthritis. Ann Pharmacother. 1997 Sep;31(9):1009-11. [PubMed:9296242 ]
  8. Van Overmeire B, Allegaert K, Casaer A, Debauche C, Decaluwe W, Jespers A, Weyler J, Harrewijn I, Langhendries JP: Prophylactic ibuprofen in premature infants: a multicentre, randomised, double-blind, placebo-controlled trial. Lancet. 2004 Nov 27-Dec 3;364(9449):1945-9. [PubMed:15567010 ]
  9. Castillo M, Smith PC: Disposition and reactivity of ibuprofen and ibufenac acyl glucuronides in vivo in the rhesus monkey and in vitro with human serum albumin. Drug Metab Dispos. 1995 May;23(5):566-72. [PubMed:7587932 ]
  10. Hockertz S, Heckenberger R, Emmendorffer A, Muller M: Influence of ibuprofen on the infection with Listeria monocytogenes. Arzneimittelforschung. 1995 Jan;45(1):104-7. [PubMed:7893261 ]
  11. Day RO, Williams KM, Graham GG, Lee EJ, Knihinicki RD, Champion GD: Stereoselective disposition of ibuprofen enantiomers in synovial fluid. Clin Pharmacol Ther. 1988 May;43(5):480-7. [PubMed:3365913 ]
  12. Trappe TA, White F, Lambert CP, Cesar D, Hellerstein M, Evans WJ: Effect of ibuprofen and acetaminophen on postexercise muscle protein synthesis. Am J Physiol Endocrinol Metab. 2002 Mar;282(3):E551-6. [PubMed:11832356 ]
  13. Laffi G, Daskalopoulos G, Kronborg I, Hsueh W, Gentilini P, Zipser RD: Effects of sulindac and ibuprofen in patients with cirrhosis and ascites. An explanation for the renal-sparing effect of sulindac. Gastroenterology. 1986 Jan;90(1):182-7. [PubMed:3079594 ]
  14. Goldenberg NA, Jacobson L, Manco-Johnson MJ: Brief communication: duration of platelet dysfunction after a 7-day course of Ibuprofen. Ann Intern Med. 2005 Apr 5;142(7):506-9. [PubMed:15809462 ]
  15. Yao M, Zhou W, Sangha S, Albert A, Chang AJ, Liu TC, Wolfe MM: Effects of nonselective cyclooxygenase inhibition with low-dose ibuprofen on tumor growth, angiogenesis, metastasis, and survival in a mouse model of colorectal cancer. Clin Cancer Res. 2005 Feb 15;11(4):1618-28. [PubMed:15746067 ]
  16. Jabor VA, Lanchote VL, Bonato PS: Enantioselective analysis of ibuprofen in human plasma by anionic cyclodextrin-modified electrokinetic chromatography. Electrophoresis. 2002 Sep;23(17):3041-7. [PubMed:12207314 ]
  17. Salas-Herrera IG, Pearson RM, Turner P: Concentration of ibuprofen in cervical mucus. J Pharm Pharmacol. 1991 Feb;43(2):142-4. [PubMed:1672904 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:
MAOB
Uniprot ID:
P27338
Molecular weight:
58762.475
General function:
Involved in oxidoreductase activity
Specific function:
Converts progesterone to its inactive form, 20-alpha-dihydroxyprogesterone (20-alpha-OHP). In the liver and intestine, may have a role in the transport of bile. May have a role in monitoring the intrahepatic bile acid concentration. Has a low bile-binding ability. May play a role in myelin formation.
Gene Name:
AKR1C1
Uniprot ID:
Q04828
Molecular weight:
36788.02
General function:
Involved in oxidoreductase activity
Specific function:
Works in concert with the 5-alpha/5-beta-steroid reductases to convert steroid hormones into the 3-alpha/5-alpha and 3-alpha/5-beta-tetrahydrosteroids. Catalyzes the inactivation of the most potent androgen 5-alpha-dihydrotestosterone (5-alpha-DHT) to 5-alpha-androstane-3-alpha,17-beta-diol (3-alpha-diol). Has a high bile-binding ability.
Gene Name:
AKR1C2
Uniprot ID:
P52895
Molecular weight:
15747.91
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Ibuprofen → 3,4,5-trihydroxy-6-({2-[4-(2-methylpropyl)phenyl]propanoyl}oxy)oxane-2-carboxylic aciddetails
General function:
Involved in peroxidase activity
Specific function:
Mediates the formation of prostaglandins from arachidonate. May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity.
Gene Name:
PTGS2
Uniprot ID:
P35354
Molecular weight:
68995.625
General function:
Involved in peroxidase activity
Specific function:
May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
Gene Name:
PTGS1
Uniprot ID:
P23219
Molecular weight:
68685.82
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular weight:
55627.365
General function:
Involved in transport
Specific function:
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloidal osmotic pressure of blood. Major zinc transporter in plasma, typically binds about 80% of all plasma zinc
Gene Name:
ALB
Uniprot ID:
P02768
Molecular weight:
69365.9